1. Field of the Invention
The present invention relates to novel substituted propargyl alcohols, novel allylic alcohols corresponding to said propargyl alcohols and novel unsaturated ketones which are structural isomers of said allylic alcohols, and the methods of production of such compounds. In still another aspect, this invention relates to novel unsaturated terpene ketones, their intermediate compounds and the production thereof.
2. Description of the Prior Art
A typical process known for the production of terpenoid compounds involves a multiple-step procedure based on the Carroll rearrangement using diketene which is a prevalent C.sub.3 chain extender or the Claisen rearrangement involving the use of isopropenyl ether. For example, the steps for the poduction of geranyl acetone starting with methyl heptenone may be illustrated as ofllows [See, e.g., J. Chem. Soc. 704 and 1266 (1940) and 570 (1941), Angewandte Chemie 72, 869 (1960), U.S. Pat. Nos. 2,795,617, 2,628,250, and 3,049,565]: ##STR5##
The chain extenders diketene and isopropentyl ether are comparatively expensive and the additional step for such a chain-extending reaction is unavoidable. In contrast, the use of the novel substituted propargyl alcohols and novel allylic alcohols of this invention are easily obtainable from inexpensive materials without the use of C.sub.3 chain extenders such as diketene and isopropenyl ether, and provide for the production of the desired terpenoid compounds in a more efficient and economical method.